Am i worrying about this unnecessarily?

It unnecessarily complicates things. 

Unnecessarily complex and not user friendly for non accountant types.

Jumping in on a medium sized deal and relying on cash flow for income feels unnecessarily risky.

Requiring the lease to be notarized is unnecessarily cumbersome.

Rolling the VA funding fee into your loan or paying it up front adds unnecessarily to your costs.Yes you'll get lots of leverage going the other ways discussed just don't forget leverage is a double edged sword and doesn't factor in things known as life. 

Would this make my accounting easier or unnecessarily more difficult?

Technically you are unnecessarily paying down the mortgage, since your tenant is already doing it for you, and just adding to "your" cost of the property. 

I'm having him send me pictures every day but since I live in AZ I only travel out there to see once a month, that is when I observed in person the beam was unnecessarily low and the floor needed to be bolstered.

From an accounting perspective, PW does have the capability to ingest bank QFX files for transactions and it only has a one way sync to any accounting platform, which is silly being that it is PW to QuickBooks.From a lead management standpoint, we are at the mercy of the useless "get more information on this listing" forms and emails we get in different forms from the Trulia, Zillow and HotPads of the world.